Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:44 UTC |
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Update date | 2024-11-29 22:27:57 UTC |
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Primary ID | FDB000846 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Vanillic acid |
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Description | Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavoring and scent agent that produces a pleasant, creamy odor. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea and vanilla-flavored confectionary. Vanillic acid selectively and specifically inhibits 5'nucleotidase activity. (PMID: 16899266). |
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CAS Number | 121-34-6 |
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Structure | |
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Synonyms | Synonym | Source |
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4-Hydroxy-3-methoxybenzoic acid | ChEBI | 4-Hydroxy-3-methoxybenzoate | Kegg | Vanillate | Generator | 3-Methoxy-4-hydroxybenzoate | HMDB | 3-Methoxy-4-hydroxybenzoic acid | HMDB | 4-Hydroxy-3-methoxy-benzoate | HMDB | 4-Hydroxy-3-methoxy-benzoic acid | HMDB | 4-Hydroxy-m-anisate | HMDB | 4-Hydroxy-m-anisic acid | HMDB | Acide vanillique | HMDB | p-Vanillate | HMDB | p-Vanillic acid | HMDB | Protocatechuic acid 3-methyl ester | HMDB | Acid, 4-hydroxy-3-methoxybenzoic | HMDB | p Hydroxy m methoxy benzoic acid | HMDB | 4 Hydroxy 3 methoxybenzoic acid | HMDB | Acid, vanillic | HMDB | Acid, p-hydroxy-m-methoxy-benzoic | HMDB | p-Hydroxy-m-methoxy-benzoic acid | HMDB | 2-Methoxy-4-carboxyphenol | HMDB | Methylprotocatechuic acid | HMDB | VA | HMDB | m-Methoxy-p-hydroxy-benzoic acid | HMDB | Vanillic acid | KEGG | 4 Hydroxy 3 methoxybenzoic Acid | biospider | 4-hydroxy-3-methoxy-Benzoate | biospider | 4-hydroxy-3-methoxy-Benzoic acid | biospider | 4-Hydroxy-3-methoxybenzoic acid (vanillic acid) | biospider | 4-hydroxy-m-Anisate | biospider | 4-hydroxy-m-Anisic acid | biospider | Acid, 4-Hydroxy-3-methoxybenzoic | biospider | Benzoic acid, 4-hydroxy-3-methoxy- | biospider | m-Anisic acid, 4-hydroxy- | biospider | P hydroxy m methoxy benzoic acid | biospider | P-hydroxy-m-methoxy-benzoic acid | biospider | P-hydroxy-m-methoxy-benzonic acid | biospider | P-vanillate | biospider | P-vanillic acid | biospider | Protocatechuic acid, 3-methyl ester | biospider | Va (van) | biospider | VNL | biospider |
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Predicted Properties | |
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Chemical Formula | C8H8O4 |
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IUPAC name | 4-hydroxy-3-methoxybenzoic acid |
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InChI Identifier | InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11) |
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InChI Key | WKOLLVMJNQIZCI-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=C(O)C=CC(=C1)C(O)=O |
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Average Molecular Weight | 168.148 |
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Monoisotopic Molecular Weight | 168.042258738 |
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Classification |
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Description | Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | M-methoxybenzoic acids and derivatives |
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Alternative Parents | |
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Substituents | - M-methoxybenzoic acid or derivatives
- Hydroxybenzoic acid
- Methoxyphenol
- Benzoic acid
- Anisole
- Phenoxy compound
- Benzoyl
- Phenol ether
- Methoxybenzene
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocarboxylic acid or derivatives
- Ether
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Foods | Cocoa and cocoa products Grains: Nuts and legumes: Fruits and vegetables: Fats and oils: Beverages: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 57.14%; H 4.80%; O 38.06% | DFC |
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Melting Point | Mp 210° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 1.5 mg/mL at 14 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | 1.43 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa2 9.39 (25°) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0gb9-6900000000-c13506201c3612fc7ca5 | 2015-03-01 | View Spectrum | GC-MS | Vanillic acid, 2 TMS, GC-MS Spectrum | splash10-0hp2-2691000000-8409d9c758b023c6576b | Spectrum | GC-MS | Vanillic acid, non-derivatized, GC-MS Spectrum | splash10-0gb9-2900000000-ccd8d4a214bc1a7f08c5 | Spectrum | GC-MS | Vanillic acid, non-derivatized, GC-MS Spectrum | splash10-0hp2-2691000000-8409d9c758b023c6576b | Spectrum | GC-MS | Vanillic acid, non-derivatized, GC-MS Spectrum | splash10-0g0b-2981000000-a58243e35d1e3a64d2aa | Spectrum | Predicted GC-MS | Vanillic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0g4i-1900000000-851f4a1738be8dd91d47 | Spectrum | Predicted GC-MS | Vanillic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00dj-7390000000-18c5f822b380ea00aa26 | Spectrum | Predicted GC-MS | Vanillic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0gb9-0900000000-0aa6709c16899e222086 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0a4i-0900000000-9aa2b9d4aa89e6ac12ab | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0a4i-0900000000-6d98ebfa89f4b8ee1e6b | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-0gb9-2900000000-babed327a6e49c6f7d51 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-014i-0900000000-105f33777cee542cf6df | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-05fr-1900000000-a502792703fa2f211035 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0a4l-5900000000-037ef32f4c68a5252b92 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0a4i-9800000000-ecd60ac022f5fee1d5ef | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-066u-9300000000-c63f7f792794f3c748a0 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-014i-0923211100-7e9f357f7429cff05524 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-014i-0923211100-7e9f357f7429cff05524 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0a4i-0429110000-57f8760ce65d48cdc01f | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0a4i-0429110000-57f8760ce65d48cdc01f | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-014i-0923211100-7e9f357f7429cff05524 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0a4i-0900000000-8e112ffa4dcc7c08b0fd | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0a4i-0429110000-57f8760ce65d48cdc01f | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0uxr-0900000000-29a2674dccd1fa478bd5 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0900000000-105f33777cee542cf6df | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-05fr-1900000000-c4ce596998934098267b | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0900000000-342964fa3647815dd1d2 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0uxr-0900000000-f16c365899f9d95733d3 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zfs-5900000000-e5593db0a935e1534bc6 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-6a1a2db582acd95348ea | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0600-0900000000-eda6cfe601d63ed00f8d | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-6900000000-b2c1e3f6b255e94a10af | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, DMSO, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, DMSO, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, DMSO, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 8155 |
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ChEMBL ID | CHEMBL120568 |
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KEGG Compound ID | C06672 |
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Pubchem Compound ID | 8468 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16632 |
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Phenol-Explorer ID | 414 |
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DrugBank ID | DB02130 |
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HMDB ID | HMDB00484 |
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CRC / DFC (Dictionary of Food Compounds) ID | BJS05-K:BJS01-G |
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EAFUS ID | 3829 |
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Dr. Duke ID | 4-HYDROXY-3-METHOXY-BENZOIC-ACID|VANILLIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002682 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1051611 |
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SuperScent ID | Not Available |
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Wikipedia ID | VA |
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Phenol-Explorer Metabolite ID | 414 |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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Aldose reductase inhibitor | 48550 | An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy. | DUKE | Allelopathic | | Biochemicals that inhibit growth, survival, or reproduction in other organisms, with potential therapeutic applications in weed control, antimicrobial, and anticancer treatments, and key medical uses in developing novel pesticides, antibiotics, and chemotherapeutics. | DUKE | Anti-helmintic | 33281 | An agent that kills or expels parasitic worms, treating helminthic infections. Therapeutically, it targets intestinal parasites, reducing infection symptoms. Key medical uses include treating roundworm, hookworm, and tapeworm infections. | DUKE | Anti bacterial | 33282 | An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis. | DUKE | Anti-cancer | 35610 | An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival. | DUKE | Anti-fatigue | 52217 | An agent that reduces physical and mental exhaustion, enhancing endurance and vitality. It plays a biological role in regulating energy metabolism and mitigating oxidative stress. Therapeutically, anti-fatigue agents are used to manage chronic fatigue syndrome, improve athletic performance, and alleviate symptoms of anemia and other debilitating conditions. | DUKE | Anti-inflammatory | 35472 | An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis. | DUKE | Anti leukemic | 35610 | An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies. | DUKE | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | Anti peroxidant | | An agent that prevents oxygen atom and peroxide formation, reducing oxidative stress and cell damage. It plays a biological role in protecting cells from free radicals. Therapeutically, it's used to manage conditions like cancer, Alzheimer's, and atherosclerosis, with key medical applications in neuroprotection, cardiovascular health, and anti-aging. | DUKE | Anti radicular | | An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management. | DUKE | Anti septic | 33281 | An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management. | DUKE | Anti-sickling | | An agent that prevents sickling of red blood cells, used to treat sickle cell anemia by reducing hemoglobin polymerization and improving blood flow, thereby alleviating associated pain and complications. | DUKE | Antitumor | 35610 | An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes. | DUKE | Antitumor promoter | 35610 | An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis. | DUKE | Ascaricide | 33281 | An agent that kills roundworms, particularly Ascaris species, playing a crucial role in treating parasitic infections. Therapeutically, it is used to eliminate intestinal parasites, reducing the risk of complications. Key medical uses include treating ascariasis, a common intestinal infection, and preventing related conditions such as malnutrition and intestinal blockages. | DUKE | Cancer preventive | 35610 | An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence. | DUKE | Choleretic | | An agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function. | DUKE | Fungicide | 24127 | An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage. | DUKE | Immunosuppressant | 35705 | An agent that suppresses the immune system, reducing inflammation and preventing rejection in organ transplants, and treating autoimmune diseases such as rheumatoid arthritis and lupus. | DUKE | Laxative | 50503 | An agent that stimulates bowel movements, relieving constipation by softening stool or increasing intestinal motility. Therapeutically, laxatives are used to treat constipation, prepare the bowel for medical procedures, and manage certain medical conditions, such as irritable bowel syndrome. | DUKE | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE | Ubiquiot | | An antioxidant that protects cells from damage, playing a crucial role in energy production. Therapeutically, it has applications in managing neurodegenerative and cardiovascular diseases, with key medical uses including reducing oxidative stress and improving mitochondrial function. | DUKE |
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Enzymes | Not Available |
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Pathways | Name | SMPDB Link | KEGG Link |
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Metabolism and Physiological Effects of Vanillic Acid | SMP0126881 | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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dairy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| milky |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| sweet |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| creamy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| powdery |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| vanilla |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| bean |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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